Borane;tetrahydrofuran → HCID 11348323, compound
Reaction equation
B.C1COCC1.[Cl:7][C:8]1[S:12][C:11]([S:13]([NH:16][C@H:17]([C:24](O)=[O:25])[CH2:18][CH2:19][C:20]([F:23])([F:22])[F:21])(=[O:15])=[O:14])=[CH:10][CH:9]=1>C1COCC1>[Cl:7][C:8]1[S:12][C:11]([S:13]([NH:16][CH:17]([CH2:24][OH:25])[CH2:18][CH2:19][C:20]([F:21])([F:22])[F:23])(=[O:15])=[O:14])=[CH:10][CH:9]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Borane-THF (1 M, 15 mL, 14.21 mmol) was added dropwise over 30 min at 0° C. to a solution of N-[(5-chlorothien-2-yl)sulfonyl]-5,5,5-trifluoronorvaline (1.0 g, 2.84 mmol) in THF (10 mL). The reaction was allowed to warm to 25° C. for 18 h and then was quenched by addition of 50 mL of 10% acetic acid in methanol. After solvent evaporation, the crude product was dissolved in EtOAc and washed with 1N HCl, H2O and saturated NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated to produce a crude oil (0.83 g) that was purified via flash chromatography, eluent: 1:6 ethyl acetate-hexane. This produced the title compound 5-chloro-N-[4,4,4-trifluoro-1-(hydroxymethyl)butyl]thiophene-2-sulfonamide as a colorless oil (0.46 g, 48%). Mass Spectrum (−ESI): 337 (M−H)−.
Workup
- customwas quenched by addition of 50 mL of 10% acetic acid in methanol
- customAfter solvent evaporation
- dissolutionthe crude product was dissolved in EtOAc
- washwashed with 1N HCl, H2O and saturated NaHCO3
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto produce a crude oil (0.83 g) that
- customwas purified via flash chromatography, eluent
Sources & evidence
- ORD record
- ord-b128f0af8fc946819899b903fc1e74a5
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07547725B2
Reaction notes
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